Methyl Acrylate → HCID 67492674, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-(2-iodophenyl)-1-methylpiperidin-4-amine (550 mg, 1.74 mmol), methyl acrylate (157 μL, 1.74 mmol), palladium acetate (39 mg, 0.17 mmol), tri-o-tolylphosphine (106 mg, 0.35) and diisopropylethylamine (608 μL, 3.48 mmol) in 7 mL DMF was deoxygenated with argon then heated at 100° C. for 5 hours. The mixture was cooled to room temperature then partitioned between EtOAc (150 mL) and H2O (20 mL). After extraction, the organic layer was separated and rinsed with brine. The organic layer was dried over Na2SO4, filtered and concentrated to give a yellow residue, which was subjected to flash chromatography on silica gel using 5%, 2M NH3 in MeOH/CH2Cl2. A viscous yellow oil was obtained (350 mg, 73.4%). 1H-NMR (CDCl3) δ 7.85 (d, J=15.9 Hz, 1H), 7.37-7.35 (m, 1H), 7.24-7.21 (m, 1H), 6.72-6.67 (m, 2H), 6.33 (d, J=15.9 Hz, 1H), 3.88-3.85 (m, 1H), 3.81 (s, 3H), 3.36 (brs, 1H), 2.84-2.81 (m, 2H), 2.31 (s, 3H), 2.18-2.05 (m, 4H), 1.63-1.51 (m, 2H). MS (ESI): 275.2 (M+1, 100%).

Provenance & Evidence